Oh Cortona...how I love thee so. Most people know of this town because of the famous book/movie from France Mayes (who still has her famed Bramasole Villa tucked up in the hills above Cortona), it's popularity shows on any day during the summer by the throngs of tourists cruising down via Nazionale. 

When I lived in Italy during my internship, Cortona was one of the easiest towns to get to from Castiglion Fiorentino. It was a convenient bus trip away from the convent when we didn't have a lunch shift, but close enough that we could get back in time to work the dinner shift! Plus at the time, the bus picked us up at the top of our hill and dropped us off at the top of Cortona in Piazza Garibaldi! Win! 

You'll hear quite a bit of English in this town too, not just from tourists. Cortona hosts a popular study abroad program for the University of Georgia. Similar to Castiglion Fiorentino, you'll find a many expats who met their spouses while studying abroad in Italy! 

While it's a lot more crowded than it used to be, Cortona is still worth a visit for some shopping, dining and sketching!